The Mysteries of Molokai 2 Oahu

Morgan Hoesterey, one of M2O’s most seasoned SUP queens, finesses across the Ka’iwi Channel.

A first-person exploration of the legendary Molokai 2 Oahu race

Words by Will Taylor
Photos by Aaron Black-Schmidt

In the center of the Pacific Ocean, in the middle of the Hawaiian islands, a lonely piece of land stands long and low against the deep blue and the wind that skates across it.

Life on Molokai is harsh.

Invasive kiawe trees stand craggily against the wind and survive in the overgrazed grasslands of the island's lower western slope. Wild turkey and axis deer wander across the road in front of vehicles then disappear in the thickets of tall grass that bends in the wind. The earth the plants grow from is a deep red. The island has just over 7,000 residents and most of those have to hustle to make a living.

Our impromptu guide in this place is Donald A. Gutierres, born in Oahu, who came here 45 years ago on a two-week vacation and never left. About 75, with waxy, tan skin and a Molokai Outrigger hat pulled down to the side to block the strong sun, Guttierres runs the MidNite Taxi, Molokai's only nighttime ride service.

"No one picks people up at night, eh," he says, his voice betraying traces of Hawaiian pidgin. "You wouldn't believe the times people call, eh."

The MidNite taxi drops us off under a canopy of overgrown trees and birds of paradise. You can smell the ocean but can't see it. We drop our stuff and wander down to the beach. Across a dark blue expanse of water, shrouded in clouds but visibly green, lies Oahu. We flew to this island from there, today. In a couple days, we'll paddle back.

Molokai is a hard place to live and even a hard place to get to, especially if you want to paddle across the channel in the infamous Molokai 2 Oahu race. I was there with my paddling partner, Morgan Hoesterey, to test ourselves in that race against the most infamous channel in paddling.

Just getting to the starting line of M2O on the last weekend of July is an accomplishment. Months of training, thousands of dollars, hours of logistics and one of the most stacked race fields in the world are all part of the deal. It's brutal. Which raises some questions: Why do people do this race? Why do they keep coming back? And why am I here in the first place?

A team closes in on Oahu as Koko Crater looms in the background.

It all started as a way to pass the time between swells. Prone paddling for exercise has always been common practice for surfers, but in the '90s, buddies Mike Takahashi, Garrett McNamara and Dawson Jones were getting after it hard. After Jones did the Catalina Classic—from Catalina Island off the California coast to Manhattan Beach on the mainland—he talked his partners into giving a race between Molokai and Oahu a try. The next year, 24 solo paddlers and eight teams lined up, looked at Oahu and after the starting gun, started paddling.

In the 20 years since its inception, Molokai 2 Oahu (M2O) has become the most prestigious paddle race in the world. It's an anomaly in the competitive paddling world, a standalone race different than all others.

Kai Lenny, venerable SUP racer, big-wave surfer and wind/kitesurf specialist puts it at the top of his list every year.

"In the winter, the most daunting thing I do is surf Jaws," Lenny says. "In the summer, the scariest thing I do is the channel. I know I'm going to push myself to my physical limit, the highest level that I can ever do."

Part of the fear is the distance: 32 miles is a long way to paddle. And this isn't any normal stretch of ocean. The Ka'iwi Channel—also known as the Channel of Bones—is revered in Hawaii for its tempestuous nature, for swallowing boats whole and even taking the lives of legendary waterman: this is where famous Hawaiian Eddie Aikau disappeared after he paddled away from the replica Polynesian sailing canoe Hokule'a in an effort to get help for the rest of his stranded crew.

"You're in the wilderness out there," Takahashi, organizer for all 20 years of the race, says. "You're trekking over liquid jungle and that's not something that's easy to find."

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Current women's SUP champion Sonni Hönscheid feels that wildness and the history every time she makes the crossing.

"Paddling has been a part of Hawaiian heritage since the Polynesians navigated through the open ocean, guided by the stars, currents and wind," she says. "I feel very honored … to experience a little part of that history, navigating using the wind, waves and current to make it to Oahu."

So before you even step in the water, there's weight, history and Hawaiian legacy there. And then there's the competition: If you're an open ocean racer, M2O is the proving grounds for what you can do. It's here that Jamie Mitchell won the crossing 10 times in a row on a traditional paddleboard. It's here that Connor Baxter and Kai Lenny have broken and re-broken the fastest SUP crossing times. It's here that Hönscheid has won three times running. It's here that Kanesa Duncan Seraphin won eight prone titles before young Australian Jordan Mercer started her six-year winning streak. It's here that more casual paddlers such as myself come to test themselves in the ultimate race.

A paddler grinds it out off China Walls, just before turning the corner to the finish line.

The race grew every year until they capped it in 2010 due to logistics (each racer or team is required to have an escort boat, accommodations on Molokai are limited and the liability for nearly 200 racers in the open ocean is a nightmare). It's so competitive to get a place in the race now that there's a lottery to even get a spot.

Part of that is because people just keep coming back. There were six people in 2016 that had raced in the first one and were racing in the 20th, including the winner of the first-ever race, traditional paddleboard legend Mick DiBetta. Another, Matt Sack, has done all 20 races on a stock prone paddleboard. That kind of dedication takes a whole life. My partner hadn't been there from the beginning but she had been the first woman to ever race across on a SUP. This would be her ninth M2O crossing.

Morgan is not good at saying no. A month before the race was supposed to start, she tried to cancel her spot, to give it to another paddler who wanted it more. She hadn't been training and she wasn't stoked. But when she went to click that button…she couldn't.

"I thought I was going to let it go and I didn't realize how important to me it was until that moment," Hoesterey says. "I almost got jealous of the pain my friends were going to experience, the stories they were going to have."

Travis Grant.

I'd originally signed up for a two-man team but when a buddy had asked to join, we'd gone up to three. When Morgan heard I was going to paddle the channel with two other people and she was going to paddle alone with almost no training, she started coercing me.

"Soooo, you've been training for a two-man crossing anyway, right?" she asked. "Maybe you should just leave your team and paddle with me." Insert cheesy grin here.

As much as I was looking forward to an easier race, I had been training hard for months. A two-person crossing had been my original goal. And I didn't want things to be too easy. A little suffering is good for the soul. Plus, Morgan and I have had some awesome adventures together. So we teamed up. Which put some extra pressure on me. After all, my partner was a person who's had a boat driver drop her off on Molokai so she could paddle back alone with just her phone and her SPOT device for safety.

"It makes you feel strong," she says. "There're not many places I feel strong in life but in that channel I feel that way. Out there I know what I'm doing."

I wasn't sure that would be the case for me.

Water World: Escort boats pair up with their racers near the start of the race.

Bacon was a bad choice. The egg and pork breakfast burrito that I'd eaten as light was creeping into the world danced poorly with the butterflies in my stomach as I wobbled on my board near the starting buoy. The best SUP paddlers in the world jockeyed for position around me: Lenny, Baxter, Grant, Hönscheid, Anderson. Nerves were high. A fan said hi to Australian pro Toby Cracknell and went to shake his hand. Cracknell balked, "Do you have suncream on your hand?" He didn't want a single thing to go wrong.

The start was chaos. It was a serious struggle to remain calm and find my own pace. There was a slight tail wind and the chop off the other paddlers' boards was intense. And damn, the pros took off like they were shot out of a gun. Still, I tried to race at my own speed and not get caught up in the moment. As the pack spread out and the escort boats found their paddlers I still wasn't feeling it. I paddled for a half hour, feeling unsteady and uncoordinated, like all my training had been for naught. I was happy when Morgan hopped off the back of the boat for her first turn on our pink, 14-foot Bark.

"It's about finishing to the best of your ability," says Jamie Mitchell. "The person that comes across that (finish) line last gets a bigger cheer than first. That's special. It changes lives."

I jumped off into the water and there I found silence. At that moment I wasn't in a race, I wasn't in between Molokai and Oahu, I wasn't anywhere. I was just a body in space.

And then I surfaced. Wind swell knocked me as I swam toward the boat and its chugging diesel engine. The wind whistled in my ears. My muscles ached from the 30-minute effort hammering amidst the chunder of mad paddlers.

I pulled myself up on the boat and turned to watch Morgan bouncing away downwind, toward Oahu. It was time to refuel and rehydrate and get ready to go again, mentally prep myself for another round with the Ka'iwi Channel. Even though I was only doing half the channel I knew it was going to take all the strength I had.

We should talk about Jamie Mitchell. Of all the people that have dedicated their lives to this channel, Mitchell has the record to top them all. Of the ten times he raced across on his unlimited traditional paddleboard, he won ten times. And he did it all in a row.

"My relationship with the channel changed over the 10 (wins)," Mitchell says. "Everybody has their own story to tell about the channel and that keeps drawing you back. You never cross the finish line knowing that you did it perfect."

While he hasn't raced in M2O since he last won in 2011 and has gone on to have a storied career in big-wave surfing, Mitchell says he'll undoubtedly be back to race in some way, shape or form, whether it's on a SUP or a relay team.

"It's a special channel," he says. "The Molokai race has given me everything. I wouldn't be here today without it."

And though he has the most wins of anyone in M2O history, Mitchell acknowledges that it's not just about being the winner or record holder.

"It's about finishing to the best of your ability," he says. "The person that comes across that (finish) line last gets a bigger cheer than first. That's special. It changes lives."

Dave Kalama, SUP pioneer, M2O SUP champion, Mitchell's good buddy and channel aficionado reckons he's raced across the channel around 35 times on SUPs, paddleboards, two-man and six-man canoes as well as on relay teams (there are outrigger competitions across the Ka'iwi as well). He knows the dedication it takes to compete out there at the highest of levels.

"The only way you can be the guy at the front is to love it," Kalama says. "You can't do it for the notoriety because it won't motivate you to sacrifice the time with your wife, your family and the surf. Your passion has to be so high. Jamie epitomizes that more than anyone."

And all the other people that have stood on top of that podium? He puts it bluntly.

"You're not going to win that race without being a tough son-of-a-bitch," Kalama says.

But it's exactly the difficulty that makes it rewarding—no matter how you cross the line.

"It's literally one of the most testing experiences you'll have in life," Kalama says. "Those moments don't come around often. You'll learn a lot about what you're made of. That can give you a lot of confidence in life."

The Ka'iwi Channel lived up to its fickle reputation as we paddled toward Oahu. For a while, the wind looked as if it was going to cooperate for an epic downwind run. Then, a series of squalls blew through and suddenly there were well-overhead swells running through the line from the north, cresting and throwing everything into chaos, the world becoming a grey, undulating mass of peaks and valleys. As soon as it looked like it was going to get really intense, the wind laid down altogether and left a bumpy, jumbled and hard-to-read ocean in its place.

It's difficult to find a rhythm in conditions like that but Morgan and I actually found the flow, switching on 20-minute intervals, which allowed us to paddle even harder during our "on" times and get a quick snack and hydrate without cooling down too much in between.

As Koko Head inched almost imperceptibly closer and the sun came out, the water below us went from blue, to bluer to the most intense blue I've ever witnessed. Morgan was well-acquainted with it.

"That's a shade of blue that you have to earn," she says. "You can see it from a boat but I don't feel like you appreciate it until you've done it under your own power."

Tag team: Morgan awaits her turn at the helm.

I took to diving underneath the ocean's surface to take a peek every time my turn was over, just to see the sun's rays refract and dance off into the deep blue. Those were my moments of peace amidst all the exertion.

It's amazing how much room there is out there, and not just below the water. The squalls had blown us on a southern line across the channel and we hardly saw another boat or paddler for hours. It was just us and the water.

That all changed as we pulled up alongside Oahu. Other paddlers and boats started to converge around us as we closed in on Portlock Point. We picked up the pace and started thinking about how we would finish amongst the other teams. Morgan decided to take a longer stretch then, so that I could experience the race finish. She hit the water hard and was looking strong. But another sideways squall howled through and beat on her as she squeezed out the last of her energy.

We switched off at China Walls, the finish line just visible far in the distance. At that point, the bump riding is over. The wind comes over the land and offshore from there, turning the finish into an upwind slog across a series of shallow reefs. It was hard for me and I'd only done half the channel. For those that had paddled the whole thing, I could see how this stretch might break you.

The team switch is tiring and exhilarating all at once.

When it was all said and done Kai Lenny had broken the unlimited SUP record (4:07:41 time—he also holds the stock, 14-foot record), Australian Matt Bevilacqua set a new unlimited paddleboard record (4:40:31) and his countryman Stewart MacLaclan set a stock paddleboard record (5:12:35). I crossed the line for our team at 5:39:32.

The scene at the finish line was a salty mix of used adrenaline, sunburnt faces, smeared race numbers, fresh leis and genuine happiness. Each paddler gets their time in the spotlight as the announcers call their name and congratulate them on their accomplishment. Beer, food and friends followed in great quantities. The camaraderie spilled out from the water onto the grass as the whole group of racers, support crews, families and organizers enjoyed their respective accomplishments.

Sitting in the shade of a palm tree, salty, noodly and happy, it was easy to see Molokai 2 Oahu is a sum of all its parts. It's undoubtedly one of the toughest races in the world, from the logistics to the length to the competition to the channel itself. The reasons paddlers keep coming back are intensely personal. Some, like Baxter, Mitchell, Hönscheid, Seraphin and Kalama, do it to test themselves against the best of the best and see how they stack up.

The author in red, one stroke closer to Oahu.

Others do it just to finish, to give it the best they have on that day and to walk away with a story. Some do it on a team so that they can have fun and enjoy the experience. Whatever the motivation, it's clear that it's something unique in the world of competitive sports.

For me, it was the depth of the blue in the channel. I've spent a lot of time out in the deep ocean and have never seen blue quite like that. Maybe it was because I was so exhausted at the end of each interval and needed more oxygen in my brain. Whatever it was, I can still recall that blue as clear as if I was out there right now.

And as for going back, I think I have to. For that blue, but also because I only did half the channel. It's calling me back, like a faint siren's voice carried on the wind, beckoning me with both pleasure and pain. I think I must. –WT